1,2-Dichloroethane → (+/-)-trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-[(S)-(-)-3-acetylthio-2-methylpropionyloxy]-2H-1-benzopyran

HRID 373341노트

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HRID 373341 반응식
[Br:1][C@H:2]1[C@H:7]([OH:8])[C:6]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:5]=2[O:4][C:3]1([CH3:16])[CH3:15].C(Cl)CCl.[C:21]([S:24][CH2:25][C@H:26]([CH3:30])[C:27](Cl)=[O:28])(=[O:23])[CH3:22]>N1C=CC=CC=1>[Br:1][C@H:2]1[C@H:7]([O:8][C:27](=[O:28])[C@H:26]([CH3:30])[CH2:25][S:24][C:21](=[O:23])[CH3:22])[C:6]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:5]=2[O:4][C:3]1([CH3:16])[CH3:15]

참가 물질

5

반응물 3

HCID 111,2-DichloroethaneHCID 6932483trans-2,2-Dimethyl-3-bromo-6-cyanochroman-4-olHCID 10954137S-(3-Chloro-2-methyl-3-oxopropyl) (S)-ethanethioate

생성물 1

HCID 86745230(+/-)-trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-[(S)-(-)-3-acetylthio-2-methylpropionyloxy]-2H-1-benzopyran수율 98.4%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a mixture of 94 g of (±)-trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-hydroxy-2H-1-benzopyran, 800 ml of ethylene chloride and 32.4 ml of pyridine was added 66 g of (S)-(-)-3-acetylthio-2-methylpropionyl chloride under ice-cooling over 5 minutes and stirred for 1.5 hours under room temperature. The reaction mixture was washed with diluted hydrochloric acid once and 10% aqueous sodium chloride solution twice. The organic layer was separated, dried over magnesium sulfate and concentrated under reduced pressure to give 139.8 g of (±)-trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-[(S)-(-)-3-acetylthio-2-methylpropionyloxy]-2H-1-benzopyran as a light yellow oily substance.

후처리

  1. temperaturecooling over 5 minutes
  2. washThe reaction mixture was washed with diluted hydrochloric acid once
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5ce8f967996c4edc9e5c322a720cee3e
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162553

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